title: Langkocyclines: novel angucycline antibiotics from Streptomyces sp. Acta 3034(*).
abstract: Langkocyclines A1-A3 and B1 and B2, five new angucycline antibiotics produced by Streptomyces sp. Acta 3034, were detected in the course of our HPLC-diode array screening. The producing strain was isolated from the rhizospheric soil of a Clitorea sp. collected from Burau Bay, Langkawi, Malaysia, and was characterized by morphological, physiological and chemotaxonomic features in addition to 16S ribosomal RNA gene sequence information. Strain Acta 3034 is closely related to Streptomyces psammoticus NBRC 13971(T) and Streptomyces lanatus NBRC 12787(T). Langkocyclines consist of an angular tetracyclic benz[a]anthracene skeleton and hydrolyzable O-glycosidic sugar moieties. The yellow-colored A-type langkocyclines differ in their aglycon from the blue-lilac-colored B-type langkocyclines. The A-type langkocycline aglycon is identical to that of aquayamycin and urdamycin A. The chemical structures of the langkocyclines were elucidated by HR-MS, 1D and 2D NMR experiments. They are biologically active against Gram-positive bacteria and exhibit a moderate antiproliferative activity against various human tumor cell lines.
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Berlin, Germany.
authors.forename: Bahar
authors.initials: B
authors.lastname: Kalyon
authors.forename: Geok-Yuan A
authors.initials: GY
authors.lastname: Tan
authors.forename: John M
authors.initials: JM
authors.lastname: Pinto
authors.forename: Cheau-Yee
authors.initials: CY
authors.lastname: Foo
authors.forename: Jutta
authors.initials: J
authors.lastname: Wiese
authors.forename: Johannes F
authors.initials: JF
authors.lastname: Imhoff
authors.forename: Roderich D
authors.initials: RD
authors.lastname: Süssmuth
authors.forename: Vikineswary
authors.initials: V
authors.lastname: Sabaratnam
authors.forename: Hans-Peter
authors.initials: HP
authors.lastname: Fiedler
mesh_terms: D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000494:pharmacology*; D004269:DNA, Bacterial / Q000032:analysis / Q000235:genetics; D004275:DNA, Ribosomal / Q000032:analysis; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D056945:Hep G2 Cells; D006801:Humans; D008296:Malaysia; D051379:Mice; D008958:Models, Molecular; D008969:Molecular Sequence Data; D041681:NIH 3T3 Cells; D009844:Oligosaccharides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D010802:Phylogeny; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D058441:Rhizosphere; D017422:Sequence Analysis, DNA; D012988:Soil Microbiology; D013302:Streptomyces / Q000145:classification* / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D009844:Oligosaccharides; D011084:Polycyclic Aromatic Hydrocarbons; D012336:RNA, Ribosomal, 16S